Dating After 50 / The Dating Files: Anthony (The One Who Worked Perfectly… Until He Didn’t)

This is the one that messes with your head a bit more than the obvious disasters.

Not the walking red flags. Not the men who reveal something alarming three messages in and save everyone time. This was worse than that, because on paper — and in practice, for quite a while — this one actually worked.

The profile made sense. Normal photos. Proper sentences. No sunglasses in every picture, no talk of “banter”, no warnings about being “drama-free”. Just enough information to think, okay, this feels promising.

The messages followed the same pattern. Easy, natural, not over-thought. The replies landed where they should, the tone matched mine, and nothing felt forced or performative. It had that quiet rhythm that’s surprisingly rare — the kind where you’re not checking the app every five minutes or wondering what you’ve accidentally implied.

Then there was the phone call.

Still good. Still easy. Comfortable pauses, shared humour, that low-key warmth that makes you think, oh… this is what it’s supposed to feel like. Not fireworks, not fantasy — just calm optimism. Enough to let your shoulders drop a bit.

So when we agreed to meet, I noticed myself doing something I hadn’t done in a while. I actually paused to think about what I was going to wear. Not in a frantic, who-even-am-I panic, but properly considering it. Choosing something that felt like me, rather than just “fine”. I even thought about the venue in the same way.

Instead of defaulting to a quick coffee — the universal low-investment, easy-exit option — I suggested a decent restaurant. Somewhere grown-up. Somewhere you sit down properly. Somewhere that says, I’m open to this being an actual evening.

That should have been the clue, really. I’d let myself lean in.

And then we met.

And it was like someone had quietly unplugged him.

He wasn’t rude. He wasn’t unpleasant. He wasn’t doing anything obviously wrong. But the man in front of me didn’t quite match the man from the messages or the phone call. The ease had gone. The energy felt thinner. Conversation didn’t quite land where it had before.

It wasn’t awkward exactly — just oddly flat. Jokes hovered rather than travelled. Eye contact came and went. It felt like trying to tune a radio that kept slipping just out of range. Close enough to recognise the song, but not close enough to enjoy it.

I kept waiting for the familiar rhythm to reappear, for the sense of recognition to click back into place. Instead, there was this growing awareness that we were two perfectly functional adults having a perfectly pleasant evening that wasn’t actually going anywhere.

That’s a surprisingly specific kind of disappointment.

Not because you desperately wanted him, but because you’d allowed yourself to believe — quietly, sensibly — that maybe the system had worked this time. That the translation from profile to message to voice to real-life human might finally hold.

And when it doesn’t, it’s strangely hard to explain without sounding ridiculous.

“He was great on paper.”“He was great on the phone.”“He was great… just not in front of me.”

There’s no villain here. No dramatic reveal. No lesson you can neatly package up. Just the unsettling reminder that chemistry doesn’t always survive the move from screen to space, and some people exist beautifully in theory but don’t quite arrive in the room.

We finished dinner politely. No tension. No awkwardness. Just a shared, unspoken understanding that this wasn’t going to continue. Later, I found myself briefly replaying it — wondering if I’d misread something, if he’d been nervous, if I’d changed, or if midlife dating is simply a series of near-misses disguised as progress. But I didn’t linger there for long.

Because sometimes nothing actually goes wrong. Sometimes everything lines up — until it doesn’t.

And that, frustratingly, is still an answer.

Join us next week to meet "James", the one on this self improvement journey.